Sodium methanethiolate → 6-Bromo-2-(4-morpholinophenylamino)quinazolin-7-ol

HRID 2079648Notes

Reaction equation

HRID 2079648 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[N:8]=[C:7]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[N:6]=[CH:5]2.C[S-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:17][CH:16]=1)[N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 671026766-Bromo-7-methoxy-N-(4-morpholinophenyl)quinazolin-2-amine

Product 1

HCID 1360299236-Bromo-2-(4-morpholinophenylamino)quinazolin-7-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0.32M suspension of 6-bromo-7-methoxy-N-(4-morpholinophenyl)quinazolin-2-amine (1.0 eq) and sodium thiomethoxide (4.0 eq) in DMF was heated to 80° C. in an oil bath for 12 h. LCMS data indicated the reaction was complete. The mixture was partitioned between ethyl acetate and water. The insoluble solid was filtered off and was rinsed with ether and air dried to give product. ES/MS m/z 401/403 (MH+).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. filtrationThe insoluble solid was filtered off
  3. washwas rinsed with ether and air
  4. customdried
  5. customto give product

Sources & evidence

ORD record
ord-7199ecd8076f4a4aa9e53711b1cfbaf6
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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